Sodium Carbonate → Methyl 2-ethoxycarbonylamino-3,3-diphenylpropanoate

HRID 2210682Notes

Reaction equation

HRID 2210682 reaction equation
Cl.[NH2:2][CH:3]([CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C(Cl)(Cl)Cl>[CH2:31]([O:30][C:28]([NH:2][CH:3]([CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:4]([O:6][CH3:7])=[O:5])=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 19379330HCID 19379330, compound

Product 1

HCID 19379388Methyl 2-ethoxycarbonylamino-3,3-diphenylpropanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 2-amino-3,3-diphenylpropanoate hydrochloride (Example 1a, 28.0 g, 96 mmol), chloroform (250 ml), and 1.0M sodium carbonate (250 ml) was added ethyl chloroformate (9.20 ml, 96 mmol). After the solution had been stirred for 18 h the organic phase was separated, washed with 10% citric acid, water, saturated brine and dried (MgSO4). After removal of the solvent in vacuo the residue was recrystallised from hot methanol to give methyl 2-ethoxycarbonylamino-3,3-diphenylpropanoate, m.p.=107°-109° C. 1H NMR (250 MHz, CDCl3) δ7.18-7.33 (10H, m), 5.12 (1H, br t, J=8.5 Hz), 4.95 (1H, br d, J=8.5 Hz), 4.40 (1H, d, J=8.0 Hz), 4.06 (2H, q, J=7.0 Hz), 3.50 (3H, s), 1.17 (3H, t, J=7.0 Hz). m/z (CI+) 328(MH).

Workup

  1. customwas separated
  2. washwashed with 10% citric acid, water, saturated brine
  3. dry with materialdried (MgSO4)
  4. customAfter removal of the solvent in vacuo the residue
  5. customwas recrystallised from hot methanol

Sources & evidence

ORD record
ord-dc3894cd2540425bbae2fbff994a0e06
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

Loading…